VP of People at Gorilla | In the pursuit of employee significance | Leadership & Career Coach | Illustrator | Corporate Hippy - views expressed here are my own

I’m a tech executive who believes the future belongs to companies that combine AI capability with human intelligence.

Not AI as a silver bullet.
Not people strategy as soft culture work.
Not simplistic “do more, faster” productivity narratives.
But practical systems that help organisations make better decisions as they scale.

I’ve spent my career building and operating those systems across people, performance, operating models, and now AI. 

The work only matters if it shows up in reality; how leaders lead, how teams decide, and how companies change without losing trust.

Most recently, I led the global People function at a Series B energy tech company and co-led our early AI rollout across governance, ethics, enablement, tooling, and experimentation. 

Alongside this, I work with founders, executives, and investors as a fractional leader and advisor. I help organisations roll out AI responsibly, navigate change, and build people systems that compound growth rather than create drag.

If you’re a founder, COO, CPO or leader trying to:
- adopt AI without breaking trust or momentum
- lead change without drowning managers in process
- scale people and operating systems that actually work in the real world.

I write and speak for you.

Things I write about:

- Practical AI adoption without hype or harm
- Where human judgment still matters in everyday AI decisions
- Leading change that creates clarity and engagement, not chaos
- People systems that support growth instead of getting in the way
- Why culture breaks during scale-ups, and how to fix it

Vanessa Monsequeira

May this be your 2026 reminder for everytime you get feedback. 

That a Frankenstein pizza is what happens when you try to implement ALL the feedback.

8 years ago, I got a performance review back.

It was good.

But different leaders wanted different things from my 360 and some of those things contradicted each other.

I was ready to become that Frankenstein pizza.

Then I talked to my mentor, a senior badass leader at the firm.

She said something that changed how I operate:

"Ness, you don't have to take all the feedback just because it's given to you."

It seems obvious now.

But back then, as a middle manager finding my footing, in a system that rewarded listening and implementation ....

Those words felt foreign ....but liberating.

Because trying to create a pizza with ALL the toppings is exhausting.

And it leaves a bad taste in your mouth and often for others too. 

The hard part was figuring  which feedback to listen to.

Here's what I started asking myself:

→ Was this given with good intention?
→ Deep down, is this what's actually holding me back?
→ Do I have capacity to implement this right now?
→ How will I close the comms loop on the feedback I don't take on now / ever?

It's taken me years of practice. I don't always get it right. 

But when I do, the outcomes are:

— Better use of my time.
— Better discernment of who I trust.
— Not running around like a headless self improvement chicken
— And growth in the direction that actually serves my goals as a leader.

So here's your 2026 reminder:
Not all feedback counts equally.
Not all feedback deserves action.

Choose your toppings wisely.

Vanessa Monsequeira - चित्रलेखा

VP of People at Gorilla | Building Employee Experience as a Product | In pursuit of making work suck less | Leadership & Career Coach | Corporate Hippy - views expressed here are my own

Meme showing a pizza topped with an entire roasted chicken, pepperoni slices, chocolate sprinkles, and colorful candy pieces. Caption reads: 'When you incorporate all the feedback from every critique.

Name the person who helped you step into your light and your power as a leader.

For me that person over the last two years has been Ruth Penfold

As a female leader in tech, the waters we swim in are different.

Through working with Ruth I:
🌱 Grew taller in moments where I felt like shrinking
🌱 Had mirror moments where I had to look at the person staring back at me and make decisions in line with my courage and integrity
🌱 Connected mind back to body - essential for every leader who wants to lead a team and workforce with engagement and integrity
🌱 Learned how to balance strength and softness as a woman of color in leadership
🌱 Navigated tough decisions and self-doubt with someone who's been there - Ruth is a former VP and CPO in tech

Importantly, growing happens together and I was part of one of the first the Women Who Lead cohort.

💜 Women Who Lead is a 12-week, high-touch leadership accelerator for women who are done playing small at work and ready to feel like themselves again - grounded, confident, powerful, whole. 

Superb for moments of transition and reinvention. It blends somatic work, identity work, and real leadership strategy so change actually sticks - in the body, not just the head.

The in-person and online catch-ups helped me breathe and realize phew it's not just me.

There were moments of shared joy, laughter, commiserations, consoling.
Women help other women rise.

And I can wholeheartedly recommend working with Ruth and the program. 

She has an incredible way of combining rational, emotional, and somatic practices in an integrated way.

🗓 If this is speaking to you run don't walk to the next cohort.
FREE taster workshop next week - Jan 12-22
https://lnkd.in/ecY4Ew62

And if you already know in your mind and your body this is for you - check out more info in the comments.

Thank you Ruth Penfold 🫶🏾🫶🏾🫶🏾

Two women taking a selfie on a city street, both smiling warmly at the camera. The woman on the left has long gray-blonde hair and wears gold hoop earrings with a beige top and crossbody bag. The woman on the right has dark curly hair and wears a black jacket. Behind them is a European-style street with outdoor café seating and storefronts. The photo captures a moment of genuine connection and joy between the two friends.

I have high idea productivity. But not all of my ideas are good.

And it’s probably driven my teams, friends, and family a little crazy over the years.

Yesterday, I shared that 2026 is my Year of Creating Space.

That’s hard to do when ideas fire at 100mph
 …and my personality says: yes, chase it, build it, implement it. NOW!!!!

My ideas don’t wait for quiet moments. They show up in meetings on walks, mid-conversations, reading, listening to podcasts, and during dinner.

If I don’t capture them, my brain keeps holding onto them loudly.

I’ve learned this from from teams I’ve led (and gentle nudges from my husband): 

👉🏾 Not every idea deserves action.
👉🏾 But most ideas do deserve to be captured.

I borrowed the Ideas Bin concept from listening to Nathan Barry, founder of Kit.

He often talks about how his “high idea productivity” can drive his team a little crazy.

Every time I hear it, I smile and think: "yep, that’s me".

So this year, I’m implementing it too.

Here’s how I’m using an Ideas Bin:
→ Capture ideas the moment they appear
→ Plan a date to revisit them
→ Then step away

Come back with fresh eyes and decide:
 → Keep in bin
 → Move to discovery
 → Time for action

The goal isn’t speed.
It’s creating space for better thinking.

If you’re smiling because you do this also generate ideas at the speed of light…
....you’re my people.

📌 I created a Notion Ideas Bin template. Feel free to use and make it your own!

Thanks again to Nathan Barry for the inspiration.

A screenshot of a Notion page titled “Ideas Bin.” At the top is a green call-out box with a lightbulb icon titled “Use this as a mental parking lot.” The text explains that people with high idea productivity should capture ideas without acting on them immediately, revisit them later, and decide whether to keep, explore, or act. Below the call-out is a table-style database listing ideas with columns for idea name, category (people, process, technology), date ideated, date to revisit, and status such as “Keep in bin,” “Move to discovery,” or “Time for action.”

I pre-order books the same way some folks invest in startups.

Because early support compounds.

Pre-orders help publishers gauge demand, secure better distribution, and give authors the momentum they need in those critical first weeks.

Since 2023, I've actively sought out and championed business books by women authors. I noticed that prior to this, women authors barely featured in my top 5 reads for the year.

So I started examining the supply and visibility of business books by women authors, the shelf space in bookshops, the top 10 lists recommended by apps, and thought leaders. 

The pattern was clear; women authors were barely featured.

Some of the sharpest thinking in leadership and organizational design is coming from women who deserve a bigger platform.

I've just pre-ordered three books I'm genuinely excited about:

📘 Purpose and Work by Jessica Zwaan - Jessica's framework around organizational archetypes of purpose (which I first saw at PX Immersive last year) is refreshingly non-performative. It's reframed how I think about purpose at work in a way that feels both fresh and obvious once you hear it.

📙 Exceptionals by Ingrid Tappin 🏳️‍🌈 -  I saw Ingrid present at the Valencia Digital Summit and again in a recent webinar. She's created an entirely new category of thinking about leadership and inclusion, one that's actually pragmatic rather than theoretical. Exceptional work in every sense.

📗 The Manager Method by Ashley Herd - Ashley's bite-sized videos and manager posts are gold. Having led people teams across several organizations, I've seen firsthand how little we talk about the day-to-day, practical side of management. Ashley fills that gap beautifully.

I track all the business books by women authors I'm reading in a Notion database. 

If you're building your 2025 reading list, these three deserve a spot.

And if you can, pre-order. It makes a real difference.


#womenauthors #leadership #culture

Three business book covers with arrows pointing to circular headshots of their authors: Purpose and Work by Jessica Zwaan, Exceptionals by Ingrid Tappin, and The Manager Method by Ashley Herd

One of the best career tools I’ve learned is choosing a “Year Of.”

This practice has guided my decisions for 7 years.

A single macro theme that acts a a north star for decisions, systems, and energy.

Looking back, it’s shaped a lot for me:

2019: The Year of Stabilization
2020: The Year of New Beginnings
2021: The Year of Growth & Learning
2022: The Year of Experimentation
2023: The Year of Deep Work
2024: The Year of Big Leaps
2025: The Year of Slow Productivity

🥁 For 2026, I’m choosing:
The Year of Creating Space.

Because my brain runs at 100 miles an hour, and space is the key to becoming more intentional.

When I don’t create space, I:
↳ do 100 things at once (and say yes too quickly)
↳ work right up to the next meeting… then rush
↳ don’t slow down enough to hear myself
↳ scroll instead of letting myself be bored
↳ overthink
↳ half-listen

How I do create space:
↳ a real morning routine (meditation + journaling)
↳ exercise with no distractions
↳ breathwork

How I’m creating space this year:
↳ speaking more slowly
↳ an “ideas bin” to park thoughts
↳ writing more for clearer thinking

Every time I name a year, the theme becomes a powerful driver of focus, reflection, and alignment.

What could your “Year Of” be in 2026

A vertical timeline graphic titled “The Year Of…?” on a black background. The timeline lists yearly themes from 2019 to 2026.
2019 is labeled “Stabilization.”
2020 is “New Beginnings.”
2021 is “Growth and Learning.”
2022 is “Experimentation.”
2023 is “Deep Work.”
2024 is “Big Leaps.”
2025 is “Slow Productivity.”
2026 appears at the bottom with question marks, indicating an open or upcoming theme.

When was the last time you trusted a leader or colleague who wasn't truthful with you?

I'm guessing never.

Every time I've seen trust erode, it's due to the usual suspects:

→ Someone held back feedback but told someone else behind the person's back. 
→ Or shared a half-truth because they didn't have the courage for a crunchy conversation. 
→ Or outright lied.

Cowardice - it's an ugly word we don't talk about enough at work and in leadership.

I don't say this to throw shade. 
We all have moments where we shy away from courage.

But as a leader? It's costing you the most valuable thing you have =  Trust.

What actually happens when trust breaks down:
→ Your team members stop trusting feedback that is useful.
→ Innovation dies because people play it safe or quite frankly because they can't be bothered.
→ Your engagement scores tank.
→ People show up but check out.
→ And eventually they leave.

Not because the work is hard.
But because they don't trust you.

There's a simple model that explains this: The Truth-Trust Cycle.

When you give a bit of truth → it creates trust
That trust makes you ready to give more truth → which creates more trust
And the cycle continues

The opposite is also true.
The moment trust is breached, people recoil and stop having real conversations.
And everyone's just performing their job, not actually doing it.

So here's your January challenge:
→ Have ONE hard conversation on a topic you've been avoiding.
→ Don't soften it.
→ Don't delay or delegate it.
→ Have it.

Because without the courage to tell the truth, you'll never build the trust your team actually needs.

And these are the actions that make work suck less.

#leadership #crunchyconversations

The Truth-Trust Cycle diagram showing a purple spiral on a light purple background. The spiral moves clockwise from the center outward, labeled: truth → trust → more truth → even more trust → even more truth → more trust, illustrating how truth and trust build upon each other in an expanding cycle. By Vanessa Monsequeira, Leadership that makes work suck less

There is a man riding a horse. 

The horse is galloping quickly, and it appears that the man on the horse is going somewhere important.

Another man, standing alongside the road, shouts, "Where are you going?" and the first man replies, "I don't know! Ask the horse!"

The late Thích Nhất Hạnh used to teach this zen story and says:

"This is also our story. We are riding a horse, we don't know where we are going, and we can't stop. The horse is our habit energy pulling us along, and we are powerless. We are always running, and it has become a habit."

--

Three weeks into January, I vowed to create space and to actually ride the horse instead of being dragged.

In past years, I've noticed a pattern:
→ The top 3 priorities become 5. Then 7.
→ "Heartbeat work" is often underestimated i.e. the essential keeping-the-lights-on stuff
→ Add generative AI to the mix, and suddenly the expectation is "more, faster."

The horse starts sprinting in multiple directions at once, and my December-to-January fresh ideas glow fades fast.

--

I've found two things that actually help me hold the reins:

1. Bi-weekly reflection (15-30 minutes)
A pause where I ask myself: "Did I choose this direction, or did the horse?"
It's the only way I've found to go slow so I can go fast again—in a direction I actually choose.

2. A Top 5 Priorities doc
A simple Notion doc with:
• 1 table for the top 5 priorities (not 7, not 10)
• 1 table for all the heartbeat work
For each priority:
• Who's the primary/secondary driver
• What is initially in and out of scope
• What "good" looks like

Then I socialize it with leadership and key stakeholders outside my area, so there are no surprises and a better way to discuss scope creep and new "quick wins." 🤮

--

Yesterday, I spent half a day offline planning H1.

Within an hour, I caught myself in classic Ness mode; front-loading way too much. The horse was already starting to bolt.

So I paused. Used my own frameworks: the Priorities doc and the Ideas Bin (the one I shared last week).

I can't promise the horse won't gallop away at different times this year. But I know I have the tools to tame it.

🐴 What helps you tame your horse? I'd love to hear what's working for you.

Black-and-white cartoon of a man clinging to a galloping horse while shouting, ‘I don’t know! Ask the horse!’ as another man on the roadside asks, ‘Where are you going?’”

Change doesn't fail because people are tired.

It fails because leaders stop leading when it matters most.

I just wrapped a discussion with a CEO who told me their organisation was "suffering from change fatigue."

I asked them: "How many times have you explained why this change matters?"

Them: "Maybe twice in the all-hands?"

Me: "There's likely your problem."

__

Over the years, I've consulted with dozens of organizations. And "change fatigue" comes up constantly. 

It's become the convenient excuse for why transformations stall. John Kotter found: 70% of change initiatives fail.I'd bet that with the acceleration of AI, it's higher now.

Multiple changes have been constant for decades.
Freeze, Change, Unfreeze change model rarely exits anymore. 

So why are we still so terrible at it?

Because most leaders don't understand (or don't want to understand) the basic building blocks of leading change.

Here's where it actually falls apart:

→ Leaders mention it once or twice in all-hands meetings, then wonder why nothing sticks
→ Leaders get defensive when feedback surfaces instead of listening and adapting
→ There's no consistent communication—just sporadic updates that create more confusion
→ The "why" disappears after the initial announcement, leaving people to fill in the blanks
→ Middle managers aren't equipped or empowered to champion the change on the ground

Meanwhile, their teams are left confused, disengaged, and exhausted.
Not from the change itself, but from the chaos around it.

Not everyone needs to love the change. 
But everyone needs to understand it.

People can handle change. 
They can't handle uncertainty, mixed messages, and confused timelines.

The fix is simpler than you think:
→ Make the process crystal clear from day one
→ Repeat the mission until you're sick of hearing yourself say it (then repeat it 10 more times)
→ Create feedback loops and actually listen without defensiveness
→ Equip your middle managers—they're your change champions, not your messengers

The gap between wanting change and leading it is where most transformations die.

Don't be the leader who announces change and disappears.
Be the one who stays in the arena until it sticks.

What's one change initiative you've seen fail—and what could leadership have done differently?

#changeleadership #leadership

Diagram titled "The surface area of change" showing three nested rectangles representing decreasing willingness to engage with change: largest section "Who wants change", medium section "Who wants to change", smallest section "Who wants to lead the change"

If we want to succeed as leaders, we have to realise that effective communication feels like overkill.

How you navigate...

→ Sharing Q1 priorities and watching blank faces nod
→ Saying "like I mentioned last week" for the third time
→ Realizing your teams are working on the wrong thing
→ Biting your tongue because you feel like a broken record
→ Getting asked a question you know you already answered

...determines whether your team actually executes, or an idea just exists.

And nobody warns you that the part of leadership that feels the most annoying, is repeating yourself endlessly. 

Yet it is actually the part that matters most.

We act like clarity is a one-time event. 

Like if you said it well enough the first time, it should stick.

The message isn't the problem. The lack of repetition is.

Communication is something you do until you're sick of hearing yourself - because that's roughly when your team is starting to actually internalize it.

When you stop too early:
→ Your team drifts off priority
→ The organisation looks disengaged
→ Your engagement scores for 'meaningful work' drop off

Not because they don't care, but because you thought 3 times was enough.

It wasn't.

I'll say it again: if we want to succeed as leaders, we have to realise that effective communication feels like overkill.

You need to say something at least 7+ times, in 7+ different ways before it actually sticks.

Here's one method and free resource to help: https://lnkd.in/e2aVW69u

Keen to hear from other leaders: how do you make your comms repetitive enough to actually land?


#leadership  #development #communicationtraining

My team doesn't listen" contrasted with "Your comms: 404 Page Not Found" - highlighting communication gaps in leadership

Kyle Thomas

Went from cubicle data entry to Uber Employee 250 & Startup Exec | Helping you land your career-accelerating role in less than 90 days | Founder & CEO of UpEmployment Accelerator

When it comes to startup job seeking everyone wants to be an early employee at a unicorn 🦄 & earn millions 💸.

But what's the secret to landing those opportunities? 

Here's a hint...

They don't come from the "traditional job search".

When I was job seeking I had no idea what I was doing, but with experience and research, I found ways to stack the deck in your favor.

That's what led me to land a job as Uber's 250th employee. 

After Uber, it's what led me to a VP role with a $100k salary increase at a Y-Combinator startup.

That's why I built Early.

Do you have amazing experience & want to take the next step to accelerate your career in a startup, but not sure where to start?

I wished that someone had a playbook for how to do that. 

It didn't exist, so I created it.

The Early Accelerator gives highly talented job seekers a complete playbook for how to land your next dream role plus accountability & a community to guide you along the way.

The program is designed to allow you to:
- 10x your job hunt efficiency
- Know where you want to go
- Build your personal brand
- Know the salary and equity you command
- Create a system to generate connections & opportunities
- Generate 100x more warm network connections
- Leverage repeatable frameworks
- Get in a peak performance state
- Create unwavering confidence
- Get to your dream role

Despite the challenging job market, we have seen incredible results.
↳ Average job searches lasting ~3 months (90 days vs US avg of 5 months).
↳ >$200k in salary increases.
↳ >$800k in equity increases.
↳ Total compensation increases of over $1M.
↳ Advancements from Manager to Department Head.
↳ Major career jumps from VP to the C-Suite.

I formalized the proven system into an easy-to-execute framework that anyone can use to land their dream job.

My mission is to help millions live extraordinary lives by accessing opportunities that change their careers forever.

You deserve to work in a job that lights you up, pays you what you are worth, and accelerates you toward your vision of your dream future.

Let's go get you that job!

So, D.M 📩 me here or email me at kyle@BeEarly.com today so we can accelerate your startup career the right way.

Stop wasting time applying to every company where you meet the minimum qualifications and learn our proven way to land your dream job!

P.S. If you're a startup job seeker looking to cut your job search in half, outperform over 95% of other candidates, and land a top startup job, click the link in my Featured Section and apply today!

Founder

I take groups of people from A to Z in their job search so they can land their dream job without applying online.

These methods took me from cubicle data entry to a job as Uber employee 250 and from unemployed to startup executive. I'm not special, I can teach you to do the same!

More than 80 startups became unicorns in 2025.

Here are 20 that are hiring 👇

1) Reflection AI 
• Stage: Series B
• Recent Raise: $2B
• Recent Valuation: $8B
• Employees: 60
• Hiring In: SF, NYC, DC, LDN

2) Lila Sciences
• Stage: Series A
• Recent Raise: $235M
• Recent Valuation: $1.26B
• Employees: 195
• Hiring In: CAM, SF, LDN

3) Tempo 
• Stage: Series A
• Recent Raise: $500M
• Recent Valuation: $5B
• Employees: 50
• Hiring In: SF, NYC, Remote

4) NewLimit 
• Stage: Series B+
• Recent Raise: $45M
• Recent Valuation: $1.6B
• Employees: 43
• Hiring In: SF

5) LangChain
• Stage: Series B
• Recent Raise: $125M
• Recent Valuation: $1.25B
• Employees: 136
• Hiring In: SF, NYC, BOS, DAL, MSP, CHI, LDN, Remote

6) ShopMy
• Stage: Series B
• Recent Raise: $70M
• Recent Valuation: $1.5B
• Employees: 140
• Hiring In: NYC, LA, AUS, Remote

7) Substrate
• Stage: Seed
• Recent Raise: $100M
• Recent Valuation: $1B
• Employees: 50
• Hiring In: SF

8) Fireworks AI 
• Stage: Series C
• Recent Raise: $250M
• Recent Valuation: $4B
• Employees: 148
• Hiring In: NYC, SM

9) Modal 
• Stage: Series B
• Recent Raise: $87M
• Recent Valuation: $1.1B
• Employees: 14
• Hiring In: NYC, SF, Remote

10) Gamma 
• Stage: Series B
• Recent Raise: $68M
• Recent Valuation: $2B
• Employees: 52
• Hiring In: SF, LA, Remote

11) MainFunc
• Stage: Series B
• Recent Raise: $275M
• Recent Valuation: $1.25B
• Employees: 40
• Hiring In: PAO

12) Luma AI 
• Stage: Series C
• Recent Raise: $900M
• Recent Valuation: $4B
• Employees: 24
• Hiring In: PAO, LA, NYC, LDN, Remote

13) Harmonic 
• Stage: Series C
• Recent Raise: $120M
• Recent Valuation: $1.45B
• Employees: 37
• Hiring In: PAO

14) Curative
• Stage: Series B
• Recent Raise: $152.55M
• Recent Valuation: $1.3B
• Employees: 2800
• Hiring In: AUS, DAL, FL, Remote

15) Heven AeroTech
• Stage: Series B
• Recent Raise: $100M
• Recent Valuation: $1B
• Employees: 67
• Hiring In: WA, VA

16) Kalshi 
• Stage: Series E
• Recent Raise: $1B
• Recent Valuation: $11B
• Employees: 75
• Hiring In: NYC, Remote

17) Unconventional AI
• Stage: Seed
• Recent Raise: $475M
• Recent Valuation: $4.5B
• Employees: 15
• Hiring In: PAO

18) Serval
• Stage: Series B
• Recent Raise: $74.82M
• Recent Valuation: $1B
• Employees: 50
• Hiring In: SF

19) Lovable
• Stage: Series B
• Recent Raise: $425.01M
• Recent Valuation: $6.6B
• Employees: 120
• Hiring In: STO, BOS, SF, LDN, Remote

20) K2 Space Corporation 
• Stage: Series C
• Recent Raise: $250M
• Recent Valuation: $3B
• Employees: 200
• Hiring In: LA, Remote

I dropped the final 5 in the comments below.

📆 Come back next Monday for another list of top startups looking for their next great hires.

Give me a follow, (Kyle Thomas) so you don’t miss it.

Go get that job and build something awesome 💪

♻️ Share this to help startup job seekers find a new role.

I Teach Ambitious Startup Job Seekers How To Land Career-Accelerating Roles at World-Changing Startups | “De-Risk” the Search w/ Proven Methods & Investor-Grade Data | Apply to our Startup Job Search Accelerator Below

If you’re job-searching in 2026, start here: 

These are my top 7 most useful posts of the year, distilled into one list.

1. Interviews are won in advance

The separation is in the preparation.

Use AI to simulate interviews, identify doubts, and rehearse answers out loud.

The people who practice the most win the most.

Post: https://dub.sh/2syNUyQ

2. Top candidates don’t just apply, they make the team feel something

They research deeply, understand the product, the priorities, and the people.

They walk into the interview already feeling like part of the team.

Post: https://dub.sh/Ldadro6

3. Scrolling job boards is fake work

Build an AI-driven newsfeed that surfaces roles, angles, insights, and outreach opportunities every morning. 

Replace doomscrolling with daily momentum.

Post: https://bit.ly/K2sVVEX

4. Measure your outreach

Most people underestimate the numbers.

If your response rate is ~10%, you may need 300–800 messages to land 1 offer.

Don’t look at the numbers as discouraging. Use them to drive commitment to action.

Once you see the math, you can stop taking rejection personally.

Post: https://dub.sh/PkyI6K2

5. If your job search has stalled, you haven’t failed - you’ve stopped experimenting

Most people repeat the same 3 tactics and expect new results.

Try 50 micro-experiments instead.

Track what works, adapt, iterate.

Post: https://dub.sh/2YXxqoT

6. Creativity wins, sloppiness loses

Creative applications stand out, but a lack of attention to detail kills your chances instantly.

One Early member got an offer after spending $11 on a bus ticket to record a personalized video for a startup.

Post: https://dub.sh/soykHKH

7. Momentum > motivation

Job searches get overwhelming.

Build micro-habits: move your body, send the message, ask for help, revisit your “why.”

Progress compounds.

Post: https://dub.sh/NmDNmpP

Yes, these were my top posts of the year.

But they were also the lessons that actually moved people into new roles, new industries, and new opportunities.

If you found this helpful, follow me, Kyle Thomas.

2026 is going to be packed with even more value-dense, practical, and brutally honest job search frameworks to help you land the role you want.

📌 𝗦𝗮𝘃𝗲 𝘁𝗵𝗶𝘀 𝗽𝗼𝘀𝘁 - you’ll want it when your next interview loop starts.

👋 𝗙𝗼𝗹𝗹𝗼𝘄 𝗺𝗲, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

✉️ 𝗪𝗮𝗻𝘁 𝗰𝗹𝗮𝗿𝗶𝘁𝘆 𝗼𝗻 𝘆𝗼𝘂𝗿 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵? DM me to learn how Early can support you.

AI should make your job search faster - not soulless.

I was chatting with a hiring manager of a rapidly growing Series C startup about a position she was looking to fill.

This company has: 

- $78M raised to date
- A>$450M valuation
- Multi-time founders with successful exits
- Top VC investors

“We generally look for a cover letter of someone really saying why they’re interested in [COMPANY]. I reject people who have AI-written cover letters. It’s an initial screener of whether or not this person cares enough to be here.”

This quote is word-for-word from the conversation.

AI is one of the most powerful tools in your job search, but only if you use it properly.

Used Well: It helps you find roles faster, prepare smarter, research deeper, and articulate your strengths clearly.

Used Poorly: It makes you look generic, lazy, and un-hirable.

Here are the dos and don’ts of using AI in your job search so you get the speed without losing the human connection.

𝗔𝗜 𝗗𝗼’𝘀:

- Use AI to scrape job boards to find roles and score them against your ideal job
- Use AI to research companies, founders, product roadmaps, and competitors
- Let AI help you structure your stories, case studies, and portfolio work
- Let AI help you draft thinking (think bullets), not your final messaging
- Use AI to simulate interview scenarios and rehearse answers
- Ask AI to identify interviewer doubts based on your résumé

𝗔𝗜 𝗗𝗼𝗻’𝘁𝘀:

- Don’t publish raw AI output without editing it heavily in your voice
- Don’t submit AI-written cover letters or outreach messages
- Don’t think AI auto-apply bots will land you a great role
- Don’t outsource your thinking, only your processing
- Don’t use generic prompts with no context
- Don’t rely on AI as your personality

AI is an amazing co-pilot. 

But it is far from being your replacement.

Used well, it helps you be more efficient and speeds up mundane tasks.

But used poorly, it’ll ruin your search and remove you from opportunities or relationships that could have dramatically accelerated your career.

Don’t let laziness be your downfall.

Use it to remove the mundane, think sharper, prepare smarter, and move faster than other candidates - not to copy-paste your way through the process.

📌 𝗦𝗮𝘃𝗲 𝘁𝗵𝗶𝘀 𝗽𝗼𝘀𝘁 - you’ll want it when your next interview loop starts.

👋 𝗙𝗼𝗹𝗹𝗼𝘄 𝗺𝗲, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

✉️ 𝗪𝗮𝗻𝘁 𝗰𝗹𝗮𝗿𝗶𝘁𝘆 𝗼𝗻 𝘆𝗼𝘂𝗿 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵? DM me to learn how Early can support you.

Burnout isn’t caused by work.

It’s caused by the 𝘸𝘳𝘰𝘯𝘨 work.

Most people think they’re exhausted because they’re overworked.

But the truth is far simpler:

When your job drains you, 4 hours feels like 14.

When your job energizes you, long days feel light.

During my career, I’ve lived both versions.

I started out working in a cubicle data-entry job.

Clocked in at 9 am. Clocked out at 5 pm.

And I was dead tired before, during, and after work.

Not because it was “hard.”

But because it gave me nothing back.

Then I joined Uber in the early days.

I’d get in at 8 am and leave at 11 pm some nights -

and I had 𝘮𝘰𝘳𝘦 energy than I’d ever had in my life.

Same body. Same brain. Different work.

Here’s what nobody tells you:

Good work gives energy, but bad work steals it.

And your body knows the difference long before you admit it.

If you wake up every day needing caffeine just to feel human…

it’s not a coffee problem.

It’s a career problem.

You deserve work that fills your cup, not empties it.

When did you realize an old role was draining you? 
Drop it below 👇🏻 Lets talk about it.

📌 𝗦𝗮𝘃𝗲 𝘁𝗵𝗶𝘀 𝗽𝗼𝘀𝘁 - you’ll want it when your next interview loop starts.

👋 𝗙𝗼𝗹𝗹𝗼𝘄 𝗺𝗲, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

✉️ 𝗪𝗮𝗻𝘁 𝗰𝗹𝗮𝗿𝗶𝘁𝘆 𝗼𝗻 𝘆𝗼𝘂𝗿 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵? DM me to learn how Early can support you.

If I had to start from scratch, I wouldn’t touch my résumé.

This is what I’d do instead 👇🏻

After coaching hundreds of startup candidates, the fastest path into a great startup role always follows the same shape:

Less résumé polishing.

More relationship building, clarity, and conversations.

Here’s exactly how I’d structure my job search, week-by-week, if I was starting today:

𝗪𝗲𝗲𝗸 𝟭 - I’d prep for rejection & get clear on what I want

→ Reset my mindset and limiting beliefs
→ Expect rejection (it’s part of the game)
→ Define what I want & the exact role characteristics I’m targeting

Clarity comes before momentum.

𝗪𝗲𝗲𝗸 𝟮 - I’d build confidence

→ Benchmark comp (what I could earn)
→ Refine my “About me” story (my hero’s journey)
→ Review my highlight reel of accomplishments
→ Refresh LinkedIn & résumé, so they speak directly to those roles
→ Build my target startup list

Confidence is the second step in a strong job search foundation.

𝗪𝗲𝗲𝗸 𝟯 - I’d create opportunities instead of waiting for them

→ Start with my warm network
→ Then cold outreach to people in target companies
→ Ask real questions, share interests, and engage publicly on LinkedIn
→ Show up where they hang out (online & in person)
→ Look for ways to deliver even small amounts of value

Early connection is more powerful than applications.

𝗪𝗲𝗲𝗸 𝟰 - I’d apply & prep before interviews get booked

→ Apply to companies that match my ideal job description
→ Never “just apply”, pair it with outreach & value
→ Do deep research on the company (yes, using AI)
→ Practice stories out loud, identify gaps, prep examples

Interview prep is 10x easier when you do it before you’re stressed.

𝗪𝗲𝗲𝗸 𝟱 - I’d follow up like a top candidate

I’d send value deliverables:

→ Insights
→ 30-60-90 ideas
→ Product thoughts
→ Short frameworks
→ Connections to my network

Be politely persistent.

Show excitement, agency, & what you’re capable of.

𝗪𝗲𝗲𝗸 𝟲 - I’d convert the momentum

→ By now, I should be in conversations.
→ I’d prepare for each one like it’s my last.
→ I’d demonstrate excitement + impact with examples, case studies, past wins, and mini-deliverables.

𝗪𝗲𝗲𝗸 𝟳 - I’d evaluate & refine

→ Track what worked.
→ Track what didn’t.
→ Update messaging.
→ Repeat what performed well.

Consistency compounds.

𝗪𝗲𝗲𝗸 𝟴 - I’d keep going

Applications + outreach + value delivery.

This is the system that lands outsized opportunities.

If you follow this 8-week plan, your job search becomes a system, not chaos.

This is the exact roadmap I’ve seen help hundreds of candidates land roles at companies they once thought were out of reach.

Commit to it. Stay consistent. Track it. Improve faster than 90% of job seekers.

📌 Save this post - you’ll want it when your next interview loop starts.

👋 Follow me, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

✉️ Want clarity on your job search? DM me to learn how Early can support you.

For the love of all that is good, stop clicking “Easy Apply”.

I get it, it makes you feel productive.

You’re tired, you’re stressed, and hitting one button gives you that tiny dopamine hit that says, “At least I did something today.”

But here’s the truth that no one wants to hear:

The Easy Apply button is a trap.

It feels like progress, but it puts you in the same pile as 1,200 other candidates, most of whom also didn’t read the job description.

And with AI tools now submitting 50+ applications per minute, you’re competing in a volume game you simply cannot win.

If you want to work in startups, spamming the Easy Apply button is the worst strategy you can choose.

Startups don’t hire people who blend in.

They hire people who stand out.

The ones who are excited, passionate, sharp, opinionated, action-oriented, and creative.

And you can only show those qualities by being intentional.

𝗛𝗲𝗿𝗲’𝘀 𝘄𝗵𝗮𝘁 𝗮𝗰𝘁𝘂𝗮𝗹𝗹𝘆 𝘄𝗼𝗿𝗸𝘀:

↳ Instead of 40 easy applies → pick 5 roles you genuinely want.

↳ Instead of spraying resumes → deeply research the company, product, and team.

↳ Instead of hoping the algorithm boosts your application → message the hiring manager, founder, and anywhere from 5-20 people on the team.

↳ Instead of generic cover letters → send a short, sharp note about why you’re excited and exactly how you’ll add value, and include a link to a Loom video of you speaking about why you’re a good fit.

↳ Instead of waiting → build one thing that proves you can do the role.

In a world where applying takes three seconds or less, effort and “human-ness” are the differentiators.

When you apply intentionally, people notice.

When you reach out like a human, people respond.

When you make it clear you understand the role and the company, people take you seriously.

Easy Apply helps you feel busy, but it’s intentionality that gets you hired.

If you can replace 60 minutes of scrolling with 60 minutes of targeted outreach, research, and personalized messages, you will outrun 99% of candidates in this market.

Trust me when I say - your next role 𝘞𝘖𝘕’𝘛 come from a button.

It’ll come from clarity, effort, and showing up like someone a founder or executive would actually want to hire.

📌 𝗦𝗮𝘃𝗲 𝘁𝗵𝗶𝘀 𝗽𝗼𝘀𝘁 - you’ll want it when your next interview loop starts.

👋 𝗙𝗼𝗹𝗹𝗼𝘄 𝗺𝗲, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

✉️ 𝗪𝗮𝗻𝘁 𝗰𝗹𝗮𝗿𝗶𝘁𝘆 𝗼𝗻 𝘆𝗼𝘂𝗿 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵? DM me to learn how Early can support you.

Most job searches fall apart because everything happens at once:

Applications, outreach, interviews, self-doubt, urgency

Landing a start-up role isn’t about having the best-looking résumé.

It’s about running a 𝘀𝘁𝗿𝘂𝗰𝘁𝘂𝗿𝗲𝗱 𝘀𝘁𝗮𝗿𝘁-𝘂𝗽 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵 𝗮𝗻𝗱 𝗳𝗼𝗰𝘂𝘀𝗶𝗻𝗴 𝗼𝗻 𝘁𝗵𝗲 𝗶𝗺𝗺𝗲𝗱𝗶𝗮𝘁𝗲 𝗺𝗼𝘀𝘁 𝗶𝗺𝗽𝗼𝗿𝘁𝗮𝗻𝘁 𝘁𝗵𝗶𝗻𝗴.

Often members join Early with no system… just scattered effort.

The people who succeed in landing great startup roles don’t necessarily work harder. 

They follow a 𝗰𝗹𝗲𝗮𝗿 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵 𝗽𝗹𝗮𝗻, broken into stages.

They know when to get clear on the role they want. When to build momentum through outreach and conversations. And when to convert trust into offers.

That’s exactly what the 𝟯𝟬–𝟲𝟬–𝟵𝟬 𝗱𝗮𝘆 𝘀𝘁𝗮𝗿𝘁𝘂𝗽 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵 𝗽𝗹𝗮𝗻 is designed to do.

It turns your job search from:

 • scattered → focused
 • reactive → intentional
 • emotional → manageable

Once you have a system, you stop asking:

“Am I doing enough in my job search?”

And start asking:

“Am I doing the right thing 𝘢𝘵 𝘵𝘩𝘪𝘴 𝘴𝘵𝘢𝘨𝘦?”

That shift is what helps candidates land startup roles faster without burning out or second-guessing every move.

📌 𝗦𝗮𝘃𝗲 𝘁𝗵𝗶𝘀 𝗽𝗼𝘀𝘁 - you’ll want it when your next interview loop starts.

👋 𝗙𝗼𝗹𝗹𝗼𝘄 𝗺𝗲, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

✉️ 𝗪𝗮𝗻𝘁 𝗰𝗹𝗮𝗿𝗶𝘁𝘆 𝗼𝗻 𝘆𝗼𝘂𝗿 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵? DM me to learn how Early can support you.

30 60 90 Day Plan

Comp can gets the offer signed.
Culture decides whether they sprint or quietly plan their exit.

Here’s the truth most founders and startup hiring managers learn the hard way:

You can’t buy anyone’s commitment.

You can’t bonus your way into long-term loyalty.

And you definitely can’t “culture-deck” your way out of a bad environment.

At early-stage Uber, none of us were printing money.

We had equity we hoped would be worth something, but… it wasn’t worth anything at the time. Nor did we have any guarantee the whole thing would work out.

And we definitely weren’t sitting on giant salaries.

I made $65k in my first role at Uber in 2013. That was an 85% increase over my prior role and ~$95k in today’s dollars (I thought I was RICH!).

There were people with degrees from Harvard and Stanford and masters degrees from top programs who were earning similar amounts.

But despite all that, we were willing to run through walls for the company.

Why?

Because we believed in the mission, the founder, and the product.

People don’t sprint because the comp is great, they sprint because the environment makes them want to show up with everything they’ve got.

𝐂𝐮𝐥𝐭𝐮𝐫𝐞 𝐢𝐬:

→ Whether the people around them are high caliber A players
→ Whether people are safe to speak honestly and critically
→ Whether there is transparency with data and progress
→ Whether the people like to see each other every day
→ Whether effort and impact are seen and recognized
→ Whether people are given autonomy to do their job
→ Whether the mission actually means something
→ Whether the team feels trusted
→ Whether credit is shared

Compensation gets all the attention.

But CULTURE gets outsized performance.

And if someone leaves because of a bad culture, guess what?

They’re gone for good.

There’s no counter-offer that fixes “I don’t want to be here anymore.”

In fact, I’ve heard SO many times, “You couldn’t pay me enough to go back there.”

But if they leave for money, and the culture was strong?

They’ll think about coming back.

I’ve seen quite a few of my early Uber colleagues leave after 4+ years at the company, only to return because they loved the culture.

People always remember where they did their best work.

📌 Save this post - you’ll want it when your next interview loop starts.

👋 Follow me, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

✉️ Want clarity on your job search? DM me to learn how Early can support you.

What to join a startup with a good chance of success?

Join a founder with a prior successful exit.

The founders of these 20 Series B startups have already had a successful exit. 

𝗧𝗵𝗲𝘆'𝗿𝗲 𝗮𝗹𝘀𝗼 𝗵𝗶𝗿𝗶𝗻𝗴 𝗻𝗼𝘄!

This week I pulled a list of startups that:
• Are backed by top investors
• Raised a Series B 4-12 months ago
• Have a founder with a previous exit
• Are growing headcount faster than any other Series B

If you're looking to join a Series B startup that's rapidly hiring, check the careers pages for these startups below.

𝘒𝘦𝘺: 𝘊𝘰𝘮𝘱𝘢𝘯𝘺: 𝘓𝘢𝘴𝘵 90-𝘥𝘢𝘺 𝘯𝘦𝘸 𝘩𝘪𝘳𝘦𝘴, # 𝘰𝘧 𝘢𝘤𝘵𝘪𝘷𝘦 𝘰𝘱𝘦𝘯 𝘳𝘰𝘭𝘦𝘴

 1. XBOW: 53 new hires, 38 openings roles
 2.  Fay Nutrition: 46 new hires, 5 open roles
 3.  Together AI: 38 new hires, 42 open roles
 4.  Levelpath: 32 new hires, 30 open roles
 5.  Monarch: 31 new hires, 7 open roles
 6. Sprinter Health: 27 new hires, 24 open roles
 7.  Savvy Wealth: 27 new hires, 16 open roles
 8.  Endor Labs: 22 new hires, 16 open roles
 9.  WorkWhile: 17 new hires, 19 open roles
10.  Tessell: 17 new hires, 15 open roles
11.  Tabs: 17 new hires, 23 open roles
12.  NetBox Labs: 16 new hires, 14 open roles
13.  Sentra: 14 new hires, 7 open roles
14.  Arena: 13 new hires, 7 open roles
15.  The Bot Company: 12 new hires, 14 open roles
16.  Archive: 11 new hires, 4 open roles
17.  GreenLite: 11 new hires, 11 open roles
18.  Aalo Atomics: 11 new hires, 22 open roles
19.  Mojo Vision: 10 new hires, 1 open role
20.  Omni: 9 new hires, 18 open roles

Go get that job and build something awesome 💪
____________

📆 Come back next Monday for another list of top startups looking for their next great hires.

Give me a follow, (Kyle Thomas) so you don’t miss it.

♻️ Share this to help startup job seekers find a new role.

Oh... and 𝗶𝗳 𝘆𝗼𝘂'𝗿𝗲 𝗹𝗼𝗼𝗸𝗶𝗻𝗴 𝗳𝗼𝗿 𝘆𝗼𝘂𝗿 𝗻𝗲𝘅𝘁 𝘀𝘁𝗮𝗿𝘁𝘂𝗽 𝗿𝗼𝗹𝗲, 𝘀𝗵𝗼𝗼𝘁 𝗺𝗲 𝗮 𝗗𝗠. 

We just had someone join our program and land a job at a top Series B startup in 𝗷𝘂𝘀𝘁 𝟮𝟳 𝗱𝗮𝘆𝘀.

You’re treating LinkedIn like a social media profile.

It’s not.

Your LinkedIn page is a sales landing page and LinkedIn is the search engine.

Here’s how to rank higher in the job search in just 1 hour.

1. 𝗦𝘁𝗮𝗿𝘁 𝘄𝗶𝘁𝗵 𝘆𝗼𝘂𝗿 𝗵𝗲𝗮𝗱𝗹𝗶𝗻𝗲, 𝗶𝘁 𝗱𝗼𝗲𝘀 𝟴𝟬% 𝗼𝗳 𝘁𝗵𝗲 𝘄𝗼𝗿𝗸.

If it’s vague, generic, or stuffed with buzzwords, you won’t appear in relevant searches. 

And if you do, they won’t know what the heck you do or how you fit in their org.

In 3 seconds, they should be able to tell:

 • Who you are
 • What you do
 • The results you drive
 • Who you drive them for

If that’s not the case with your headline today, change it.

Think: “Senior Startup Operations Leader | Scaling Systems, People & Processes Leveraging AI | Led the operational launch of multiple marketplaces from $0 - $500M ARR.”

2. 𝗡𝗲𝘅𝘁, 𝗳𝗶𝘅 𝘆𝗼𝘂𝗿 𝗔𝗯𝗼𝘂𝘁 𝘀𝗲𝗰𝘁𝗶𝗼𝗻.

Lead with who you are today and your mission, then back it up with proof.

Use keywords and case studies that founders and recruiters already search for: operations, product, GTM, strategy, growth, project management, AI, SaaS - whatever applies to the work you want.

(Hint: These are found in the JD, so create a long list of JDs and extract the keywords and case studies using an LLM)

Also, inject something personal. Show that you’re an actual human with real interests.

Being “passionate about process optimization“ is not a personality.

3. 𝗧𝗵𝗲𝗻 𝗴𝗼 𝗿𝗼𝗹𝗲 𝗯𝘆 𝗿𝗼𝗹𝗲, 𝗽𝘂𝗹𝗹 𝗼𝘂𝘁 𝘁𝗵𝗲 𝗾𝘂𝗮𝗻𝘁𝗶𝗳𝗶𝗲𝗱 𝗮𝗰𝗵𝗶𝗲𝘃𝗲𝗺𝗲𝗻𝘁𝘀, 𝗮𝗻𝗱 𝘀𝗵𝗼𝘄 𝗽𝗿𝗼𝗼𝗳.

Search engines love clarity.

Recruiters love impact.

Your job is to give both.

Attach links to documents, PR releases, anything that shows you actually did what you say you did.

4. 𝗔𝗳𝘁𝗲𝗿 𝘁𝗵𝗮𝘁, 𝘂𝗽𝗱𝗮𝘁𝗲 𝘆𝗼𝘂𝗿 𝘀𝗸𝗶𝗹𝗹𝘀.

Not 60 random ones.

The top 60 that map directly to the job you want.

Some recruiters use these in their search filters, but most candidates ignore them entirely.

(Hint: Remember where I told you to find these skills? In the JDs)

5. 𝗙𝗶𝗻𝗮𝗹𝗹𝘆, 𝗮𝗱𝗱 𝗮 𝗰𝗿𝗲𝗱𝗶𝗯𝗶𝗹𝗶𝘁𝘆 𝘀𝗶𝗴𝗻𝗮𝗹.

Pin a post that proves your thinking, showcases a win, or highlights a perspective that matters in your niche.

You could start a newsletter, a podcast, or share a badass proof of work example.

It’s the fastest way to turn a profile view into an outreach message.

Most people treat LinkedIn like a digital resume without realizing that founders, recruiters, and operators treat it like Google.

They search for skills, functions and people who signal credibility in the first 3 seconds.

LinkedIn itself has changed its search functionality to be more conversational and function like a search engine instead of a database with filters.

The people who win on LinkedIn aren’t the loudest, they’re the most discoverable.

👋 Follow me, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

“Do I actually want this role?”

That’s the question you need to answer honestly if you resent the pre-job assignment.

I’m talking about the case studies, presentations, and work samples as a part of the hiring process.

The hiring team didn’t create a pre-job assignment as a thoughtless hoop to jump through just to make the process harder.

It’s a trailer for the movie.

And if you hate the trailer… you’re going to hate the movie.

Assignments are the best way for the team to get an idea of what it would actually feel like to work with you.

They’re also a great way for you to stand out in the process.

They’re also a great gut check of how much you want to work there.

They show you:

 • How the team thinks
 • What problems you’ll work on
 • Whether the work energizes or drains you
 • Whether you’d enjoy doing this every day, not just once

And yes - some people argue candidates “shouldn’t have to do pre-work before speaking to a hiring manager.”

I disagree 100%.

If you want the job, you’ll do the work.

If you resent the work, you don’t want the job.

Simple.

It may sound harsh, but it shouldn’t.

Take for example Caleb Ralston. 

He has helped build the personal brands for some of the largest founder-led brands out there. 

He was recently hiring for YouTube editors, and do you know what the process looked like?

YouTube editor TRYOUTS over the course of 4 days.

Candidates needed to sign up, were sent the raw video/audio files, and had four days to edit and submit their final video edit.

No interviews before the exercise, just “show me what you got”.

Hundreds of people signed up and did the free work for the opportunity to work with one of the best out there.

And that’s the thing, if you’re not willing to do it, in this market (and in any market at most top companies), there will be people who are more than willing to do the free work.

If you find yourself procrastinating, irritated, or indifferent, that’s your signal not to push harder… but to walk away.

But if you find yourself getting curious, going deeper, losing track of time…

That’s a signal that you should lean in.

That the role might actually be right for you.

That this is work you'll enjoy, not just endure.

The pre-job assignment is a preview of the next chapter of your career.

If you hate the trailer, don’t buy the movie ticket.

If you love it, that’s your green light to go hard.

A quick aside: I know people abuse these exercises but that’s not the norm. I spoke with a new grad last week who worked 80 hours a week for two weeks for a founder on an “exercise” to build them a product. The founder even asked her to work on Christmas day. After the two weeks they shared the salary and equity and it was far lower than market rate.

So do people abuse exercises, yes. But in my experience they’re few and far between. The best companies will run you through thoughtful exercises and the exercises and “free work” are an incredible way to stand out.

Most people sabotage their startup job search by misreading silence.

Early in my career, I was wary of being annoying.

If I had a good conversation with someone and they said, “Happy to help” or “Let me look into that”, I’d leave it there.

Then a week would pass. Then two.

And then... I’d start to spiral.

 • 𝘚𝘩𝘰𝘶𝘭𝘥 𝘐 𝘧𝘰𝘭𝘭𝘰𝘸 𝘶𝘱?
 • 𝘞𝘩𝘢𝘵 𝘪𝘧 𝘵𝘩𝘦𝘺 𝘧𝘰𝘳𝘨𝘰𝘵?
 • 𝘞𝘩𝘢𝘵 𝘪𝘧 𝘐 𝘭𝘰𝘰𝘬 𝘥𝘦𝘴𝘱𝘦𝘳𝘢𝘵𝘦?

So most of the time… I didn’t. I told myself the silence meant something about me.

Everything changed once I became the “busy” person on the other side.

I loved being helpful, so I started having back-to-back calls.

 • Offering intros.
 • Promising reviews.
 • Making mental notes.

And then life happened.

Deadlines. Kids. Travel.

I forgot to follow up, this time from the other side.

My lack of action wasn’t because I didn’t care but because startups (and life) are all-consuming.

Every now and then, someone would politely follow up.

And instead of being annoyed... I loved it!

I'd take the necessary action then and there and fire a message back to the person.

That’s when it clicked.

So many people sabotage their job search because they create these elaborate stories in their head to explain the silence.

The truth is almost always, "Oops, I got super busy and forgot. Thanks for reminding me. I'll fire that off right away."

Follow up isn’t about being pushy or loud. It’s about not taking silence personally.

It’s about understanding that “no response” usually means “not right now,” not “not you.”

Some of the biggest breaks in my career came from messages I almost didn’t send.

So if you’re trying to land your next startup role, remember this:

 • Following up isn’t rude.
 • Persistence isn’t annoying.
 • Being organized is a signal of seriousness.

The people who make it aren’t the ones who never hear “no.” 

They're the ones who don't vanish just because they didn't hear back.

𝗔 𝘀𝗶𝗺𝗽𝗹𝗲 𝗿𝘂𝗹𝗲 𝗜 𝘂𝘀𝗲 𝗻𝗼𝘄 𝗳𝗼𝗿 𝘆𝗼𝘂 𝘁𝗼 𝘀𝘁𝗲𝗮𝗹: If someone offered to help and hasn't responded in 5-7 business days, I follow up once via our last method of communication (email, LinkedIn, text). I'm polite, clear, and non-apologetic. I'll do this two more times and if I don't get a response after the three messages I move on.

The moral of the story is this...

Follow up. Ask again. Stay politely persistent. 

And don't take silence personally.

📌 𝗦𝗮𝘃𝗲 𝘁𝗵𝗶𝘀 for the next time you’re debating whether to send that message.

👋 𝗙𝗼𝗹𝗹𝗼𝘄 𝗺𝗲, Kyle Thomas, for practical startup job-search strategies.

Everyone wants Olympic-level results. Most train like it’s a weekend jog.

From the outside, the people who land incredible roles look effortless.

“𝘙𝘪𝘨𝘩𝘵 𝘱𝘭𝘢𝘤𝘦, 𝘳𝘪𝘨𝘩𝘵 𝘵𝘪𝘮𝘦.”

“𝘔𝘶𝘴𝘵’𝘷𝘦 𝘩𝘢𝘥 𝘤𝘰𝘯𝘯𝘦𝘤𝘵𝘪𝘰𝘯𝘴.”

“𝘗𝘳𝘰𝘣𝘢𝘣𝘭𝘺 𝘫𝘶𝘴𝘵 𝘨𝘰𝘵 𝘭𝘶𝘤𝘬𝘺.”

But here’s what you don’t see:

The hours of preparation.

The rejections.

The setbacks.

The learnings.

The adjustments.

The quiet consistency.

When I tell my story of joining early-stage Uber, I usually give the highlight reel:

 • Quit my job in Seattle
 • Moved to New York with no network
 • Had 90 days of savings
 • Landed a role at Uber just before money ran out

But the real story looked a lot more like Olympic training:

 • Waking up at 6 am to job search (treating it like a job)
 • Getting no response from message after message
 • Long stretches where it felt like nothing moved
 • Trying to figure out the value I could provide
 • No applause, no certainty, no shortcuts
 • Dozens of awkward networking calls
 • Rejection after rejection

The truth is, the job search is an endurance sport.

In the same way, Olympians don’t control the medal; they only control their training.

You don’t get to control the output; you only control your inputs:

Your clarity, prep, networking and consistency.

And just like elite athletes, most of the progress happens long before anyone sees the result.

The people who win in this market aren’t necessarily the smartest or most connected. They’re the ones willing to put in the work when no one’s watching.

Stop chasing the podium moment and start building the systems that get you there.

If you want to land a role that changes your career, ask yourself honestly:

Are you training like an Olympian… or jogging like it’s Sunday?

What stage of your job search are you in? Comment below with a single emoji:

📖 Learning
💼 Networking
🎯 Applying
🏆 Interviewing

📌 𝗦𝗮𝘃𝗲 𝘁𝗵𝗶𝘀 𝗽𝗼𝘀𝘁 - you’ll want it when your next interview loop starts.

👋 𝗙𝗼𝗹𝗹𝗼𝘄 𝗺𝗲, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

✉️ 𝗪𝗮𝗻𝘁 𝗰𝗹𝗮𝗿𝗶𝘁𝘆 𝗼𝗻 𝘆𝗼𝘂𝗿 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵? DM me to learn how Early can support you.

I’ve helped 100+ job-seekers land roles in startups.
These are the 8 steps every successful search has in common.

You may think, “Those people are lucky.”
Right place, right time. Right connection, right company.

But after coaching hundreds of candidates, the pattern is painfully clear:
People who land great roles don’t rely on luck. 
They create luck their own luck by following a clear system.

A system that gets them unstuck when momentum dips, keeps them focused when the market feels chaotic, and helps them stand out when everyone else blends together.

Here are the 8 steps I see in every single successful search:
1. They get their mind right.

The job search is a sales process.

And in sales, there’s lots of rejection.

You have to steel yourself for the rejection to come. 

They create a plan for what it takes to get themselves into a peak state as often as humanly possible.

2. They get clarity before applying.

They define the exact role they want, why they want it, and what makes them a fit. 

“I’m open to anything” won’t cut it.

Clarity turns a chaotic search into a targeted one.

It makes every following step in the process easier and more effective.

3. They build a target company list.

Not 300 random companies, but 20-40 that match their skills, interests, and stage preferences.

This creates direction and eliminates distraction.

Batching this company/role searching also prevents random action.

4. Their LinkedIn and résumé signal credibility immediately.

They treat their LinkedIn/resume like a sales landing page crafted to stand out.

They make it clear to the reader who they are, what they do, the results they drive, and who they drive them for.

Every line is crafted to make hiring managers think: “I want to talk to this person.”

5. They track their progress

Applications, networking messages, calls, interviews, the works.

They understand what actions they’re taking.

The numbers tell them what’s working and what’s not working, and they adjust accordingly.

6. They send intentional outreach consistently.

Not mass messages.

No copy-paste templates.

Not “ChatGPT, what message should I send this person?”

High-quality messages that create genuine connection.

This is where most opportunities come from.

7. They prepare like a top candidate.

They run mock interviews, identify interviewer doubts, rehearse their stories, and study the company’s product deeply.

Most interviews are won in the prep.

8. They follow up and show real ownership.

Case studies. Value deliverables. Thoughtful notes.

They do the “free work” to show they’re operating like part of the team.

This is where offers are secured.

When you follow these steps, everything changes:

Your search stops feeling like hope.
Your outreach stops feeling random.
Your interviews stop feeling unpredictable.
And opportunities start showing up faster than you expect.

This will look like magic to those on the outside.
But you’ll know it’s a system.
And anyone can run it.

I've Helped 100+ People Land Start Up Roles

If it feels messy, you’re not doing it wrong. 

The job search is often the first real taste of start-up life. 

People think the chaos starts 𝘢𝘧𝘵𝘦𝘳 you land the role, but the interview process is just a warm-up. 

You’ll get ghosted. You’ll get rejected for reasons that don’t make sense.

A role you were excited about disappears overnight because priorities changed.

A hiring manager goes quiet because they’re juggling ten fires at once.

It’s frustrating and knocks your confidence. And it can make you start questioning yourself.

But it’s not personal, and it’s not a reflection of your ability.

It’s just how startups operate.

They move fast. They change direction. They make decisions with imperfect information.

And once you’re inside a startup, that doesn’t suddenly stop.

 • Priorities shift week to week.
 • Teams are small, so your impact (+ your mistakes) are visible.
 • Everything is an experiment.
 • You’re constantly adjusting in real time.

That’s also why the people who love startups 𝘳𝘦𝘢𝘭𝘭𝘺 love them.

They’re comfortable with ambiguity. They enjoy figuring things out as they go.

They don’t need everything to be perfectly defined to move forward.

So if you’re in the thick of the job search right now, feeling behind, dealing with setbacks, wondering if you’re doing something wrong… pause for a moment.

 Think of this process not as a punishment but as preparation.

You’re learning how to stay steady when things feel uncertain.

How to stay energized and excited while working hard.

How to keep showing up when plans change.

How to continuously experiment, measure results, and iterate. How to stay energized and excited while working hard.

How to separate noise from signal.

And guess what?

That’s exactly what you’ll need on the inside.

So keep going.

Even if “going” today just means sending one message.

Just take that first next step in the right direction.

The people who make it through the search are usually the ones built for the work.

📌 𝗦𝗮𝘃𝗲 𝘁𝗵𝗶𝘀 𝗽𝗼𝘀𝘁 - you’ll want it when your next interview loop starts.

👋 𝗙𝗼𝗹𝗹𝗼𝘄 𝗺𝗲, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

✉️ 𝗪𝗮𝗻𝘁 𝗰𝗹𝗮𝗿𝗶𝘁𝘆 𝗼𝗻 𝘆𝗼𝘂𝗿 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵? DM me to learn how Early can support you.

How long has your startup job search taken so far?

There’s no “normal” timeline - everyone’s path looks different.

But understanding the range helps you see you’re not behind… you’re human.

How long has your startup job search taken so far?

What does it actually take to break into an AI startup as a TPM?

In this case: 287 cold messages, 1 strategy, and 3 frameworks anyone can copy.

This is Amr’s story, and it’s a perfect example of what happens when someone stops treating a job search like guesswork and starts approaching it like a system.

Five months ago, Amr joined Early with one clear goal: get a Technical Program Manager role.

Not “see what comes up” or “apply generally.” He chose the role deliberately, built toward it, and committed to doing the work most people avoid.

Along the way, he used three frameworks that completely changed his results - and anyone reading this can copy them.

1. Treat outreach like a game and track your numbers.

Most people rely on feelings when they job search. 

“It feels like no one is replying.” 

“It feels like my messages aren’t working.”

Feelings are unreliable. Data isn’t.

Amr sent 287 cold messages. His response rate was 14%. His call rate was 26%.

By tracking the numbers, he could see exactly what was working, which messages landed, and where to double down.

The lesson: you can’t improve what you don’t measure. Treat it like a continuous game.

2. Personalize your outreach using your real interests.

Personalization isn’t forced flattery or dropping someone’s name into a template. It’s creating a REAL human connection.

Earlier in the year Amr visited the Rocky Mountains for the first time and absolutely loved it.

Whenever he reached out to someone based in Colorado, he mentioned that trip.

This wasn't some sort of trick or tactic. He genuinely wanted to share how much he loved the area. 

Guess what? 

That human touch dramatically increased replies.

Most people send messages that read like AI wrote them. Amr made sure he sounded like a real person.

3. Reach out to multiple people at the same company.

This is the most uncomfortable step, but also the most effective.

For the TPM role, Amr didn’t message one person - he messaged nine.

Four replied. Three had conversations with him. One referred him internally.

When you rely on a single point of contact, your chances are low.

When you create multiple internal touchpoints, you drastically increase your referral chances.

This is how applications get resurrected, moved forward, or re-reviewed even after initial rejection.

Amr didn’t get lucky. He built a repeatable system that made success inevitable.

TL;DR: Track your outreach so you know what’s actually happening. Personalize your messages so people want to reply.

Send multiple messages to people at the companies so you’re not depending on one person’s kindness.

You don’t need dozens of people to say yes, you need one. And these three frameworks dramatically increase your odds of getting it.

📌 Save this post - you’ll want it when your next interview loop starts.

👋 Follow me, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

In 2026, being qualified isn’t enough.

Hundreds of qualified applications are being submitted for every role even at startups most people have never heard of.

I was speaking with a VC Head of Talent and she said several of their portfolio companies (we’re talking tiny, early-stage, low-visibility startups) now get hundreds of applicants per role.

Not because the roles are special, and not because the comp is outrageous.

But because the volume of people applying has exploded and the use of AI tools and bots has made it even worse.

Being qualified gets you into the pile, but it won’t get you into the room.

Only visibility can do that.

I saw this again with a candidate I coached. 

Brilliant background. 
Great skills. 
Perfect match on paper.

He’d applied to ~60 roles with almost no traction.

Except one.

For that one role, he reached out directly.

He wrote a personal note, sent it to the founder, a recruiter, and a few people on the team. 
He showed them why he cared.
He made himself visible.

And instantly, he moved forward.

Here’s why visibility wins:

𝟭. 𝗩𝗶𝘀𝗶𝗯𝗶𝗹𝗶𝘁𝘆 𝗳𝗼𝗿𝗰𝗲𝘀 𝗱𝗶𝗳𝗳𝗲𝗿𝗲𝗻𝘁𝗶𝗮𝘁𝗶𝗼𝗻.

Everyone is qualified, but very few take the time to write personal messages, share context, or reach out to internal stakeholders.

When you do, you’re no longer competing with the full pile. 

You’re competing with the handful who bothered to do a little bit more work.

𝟮. 𝗩𝗶𝘀𝗶𝗯𝗶𝗹𝗶𝘁𝘆 𝘀𝗶𝗴𝗻𝗮𝗹𝘀 𝗶𝗻𝘁𝗲𝗻𝘁.

If you send a thoughtful note to the hiring manager, you’re no longer “one of 300 applicants.”

You’re a real human who cares about their mission and what they’re building and wants to help.

Founders, recruiters and teams notice it.

Trust me, I have the receipts. 

Dozens of messages from recruiters and hiring managers saying, “Wow, this is a really unique way you reached out. It really made you stand out.”

𝟯. 𝗩𝗶𝘀𝗶𝗯𝗶𝗹𝗶𝘁𝘆 𝗼𝗽𝗲𝗻𝘀 𝗱𝗼𝗼𝗿𝘀 𝘁𝗵𝗮𝘁 𝗿𝗲𝘀𝘂𝗺𝗲𝘀 𝗰𝗮𝗻’𝘁.

Referrals.
Internal conversations.
Warm intros.

The thing that moves you forward is you making yourself known to the people who matter.

So in 2026, the question isn’t:

“Am I qualified?”

It’s:

“Have I made myself visible to the people making the hiring decision?”

If not, the most talented version of you will stay buried under 300 other clicks on “Apply.”

The candidates who win this year will be the ones willing to reach out, write personal notes, send value, and make themselves impossible to ignore.

📌 𝗦𝗮𝘃𝗲 𝘁𝗵𝗶𝘀 𝗽𝗼𝘀𝘁 - you’ll want it when your next interview loop starts.

👋 𝗙𝗼𝗹𝗹𝗼𝘄 𝗺𝗲, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

✉️ 𝗪𝗮𝗻𝘁 𝗰𝗹𝗮𝗿𝗶𝘁𝘆 𝗼𝗻 𝘆𝗼𝘂𝗿 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵? DM me to learn how Early can support you

You think you’re being judged on your answers.

Founders are actually judging your signals.

Interviews, especially in startups, aren’t exams, they’re calibration exercises.

Most candidates show up obsessing over “saying the right thing.”

Meanwhile, founders are watching for something completely different:
Your signals.

And if you learn how to control the signals you send, your interviews instantly feel easier, clearer, and more predictable.

Here are 5 signals founders are judging, and how to nail each one:

1. How you react to friction.

There is no "standard startup interview process".

Hiring in startups can be messy, so expect more friction than a normal interview process.

More rounds. Trial tasks. Follow-ups. Unclear next steps.

If you expect this level of friction instead of being surprised by it, you stay composed while everyone else spirals.

Signal: resilience, realism, emotional steadiness.

2. Prepare like an interviewer

Founders want someone who understands and is excited about the product, the market, and - ideally - them.

Research the company like you’re the one hiring.

It may sound crazy, but people who share excitement about their product and the team are rare.

Signal: high-agency thinking, ownership, genuine interest.

3. Confidently show your strengths

Interview answers matter, but founders are tuning into:

– How you think
– What results you’ve produced
– What problems you can take off their plate

Be able to not only share what you've done, but how that experience tracks directly to what they need.

Signal: clarity, competence, self-awareness.

4. Understand that roles evolve

It is not abnormal for the original job description to change.

Funding, market dynamics, team changes, and strong candidates change quickly and can change what the company needs.

If you can articulate what additional value you bring, you’ll stand out instantly.

Signal: adaptability, initiative, strategic thinking.

5. Fix your mindset

The best interviewers aren’t rigid.

They’re calm, flexible, curious, and collaborative.

Going in with “I hope they like me” energy kills your performance.

Signal: confidence without ego.

The more you master these signals, the easier interviews become - not because you’ve memorized better answers, but because you’re playing the same game the founder is.

As someone who’s been on the hiring side:

Founders aren’t looking for perfection, they’re looking for patterns.

Do you think clearly?

Can you handle ambiguity?

Will you take ownership without needing permission?

Do you bring something the team doesn’t currently have?

Can you grow as fast as the company grows?

These signals tell founders far more than any polished answer ever will, and once you understand that, interviews become less about performing…

and more about demonstrating how you operate.

👋 Follow me, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

Your job search feels harder when your mind is scattered. Here’s how to steady yourself without hacks.

Drowning in options? → Get quiet and write down your top 3 priorities.

Low energy? → Read something that inspires you - a founder story, a memoir, a lesson learned the hard way.

Afraid of rejection? → Send the message anyway. Fear fades after action.

Feeling stuck? → Step away from the screen and go outside. Change your environment.

Mentally foggy? → Sleep. Nothing beats rest for clarity.

Unsure what to do next? → Ask someone who’s one step ahead. Borrow their perspective.

Frustrated? → Move your body. Motion creates momentum.

Burning out? → Stop. Take a full day off. Recovery is a strategy.

Losing patience? → Look at how far you’ve come since day one.

Struggling to stay motivated? → Reconnect with your why. The job is the outcome, your reason is the fuel.

The job search isn’t won by intensity.

It’s won by consistency.

What’s one tiny habit that helps you stay focused, in the job search or in life?

Share it below so someone else can use it tomorrow.

📌 𝗦𝗮𝘃𝗲 𝘁𝗵𝗶𝘀 𝗽𝗼𝘀𝘁 - you’ll want it when your next interview loop starts.

👋 𝗙𝗼𝗹𝗹𝗼𝘄 𝗺𝗲, Kyle Thomas, for practical startup job-search strategies + weekly curated job lists.

✉️ 𝗪𝗮𝗻𝘁 𝗰𝗹𝗮𝗿𝗶𝘁𝘆 𝗼𝗻 𝘆𝗼𝘂𝗿 𝗷𝗼𝗯 𝘀𝗲𝗮𝗿𝗰𝗵? DM me to learn how Early can support you.

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